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Andy Murray smashed his racquet after suffering an agonising opening-round defeat by Australian Alex de Minaur at the Paris Masters.
The 36-year-old fell 7-6 (7-5) 4-6 7-5 to the world number 13, who he has never managed to beat in six meetings.
Murray twice served for the match and missed match point in another gruelling contest lasting just over three hours.
It means the Scotsman has still not won a match at the Paris Masters since winning the tournament in 2016.
Murray, who has lost five of his last six matches, failed to convert three match points against De Minaur in Beijing last month and this latest loss in Paris is his fourth against the 24-year-old this year.
His opponent saved set points before pinching a close opening set with a narrow tie-break victory.
Murray recovered with a more assured performance in the second, breaking in the ninth game to level and force a decider.
Murray’s record against De Minaur this year also includes defeats at Monte Carlo and Queen’s, but it looked like the former world number one might break that losing streak after finding himself a double break up in the deciding set.
He had match point at 5-4 but missed it with a long return and smashed his racquet on the floor in anger after handing De Minaur a break-point opportunity, which he took to level at 5-5.
Murray became increasingly exasperated as he knocked the drinks bottles and towel off his bench before failing to hold either of his next two service games and squandering opportunities to force a final set tie-break.
He again smashed his racquet on the floor as he sent a return into the net and De Minaur closed out the win.
Fellow Briton, Cameron Norrie, pulled out of the tournament with a knee injury but is expected to be fit enough for the Davis Cup Finals on 23 November.
World number one and two Novak Djokovic and Carlos Alcaraz received first-round byes and will enter the tournament in the second round along with the six other top seeds.
